20. Bobby Caldwell
Funkiest Jam: Bobby Caldwell "What You Won't Do For Love"
Bobby Caldwell is best known for "What You Won't Do For Love," but that song almost didn't happen. Once he signed to Miami's TK Records, home of bands like KC & the Sunshine Band, he wrapped up his debut album but was told by the owner of the label that he didn't "hear a hit." Bobby returned to the studio and came back out with "What You Won't Do For Love." To ensure airplay on R&B radio stations, Caldwell's management tried to hide/downplay the fact that he was white by showing him only in silhouette and hiding his face. This charade lasted only until he did his first live performance.
In addition to having one of the most beautiful heads of hair in the history of the music industry, Bobby has also been sampled on several occasions, by artists ranging from 2Pac to Da Brat, Mariah Carey, Notorious B.I.G., 112, and Aaliyah. Just try to toss on "What You Won't Do for Love" and not start feeling libidinous. We've tried. It's impossible.